The crystal structure of 3-chloro-2-(4-methylphenyl)-2H-pyrazolo[3,4-b]quinoline

Abstract

In the molecule of 3-chloro-2-(4-methylphenyl)-2H-pyrazolo[3,4-b]quinoline, C17H12ClN3, (I), the dihedral angle between the planes of the pyrazole ring and the methylated phenyl ring is 54.25 (9)°. The bond distances in the fused tricyclic system provide evidence for 10-π delocalization in the pyrazolopyridine portion of the molecule, with diene character in the fused carbocyclic ring. In the crystal, molecules of (I) are linked by two independent C - H⋯N hydrogen bonds, forming sheets containing centrosymmetric R22(16) and R64(28) rings, and these sheets are all linked together by π-π stacking interactions with a ring-centroid separation of 3.5891 (9) Å.